Asymmetric Catalytic Coupling of Organoboranes, Alkynes, and Imines Possessing a Removable (Trialkylsilyloxy)ethyl Group - Direct Access to Enantiomerically Pure Primary Allylic Amines

Angewandte Chemie 43(30), 3941-3944, DOI: 10.1002/anie.200460044

The aryl substituent on the catalyst is central to the success of the title reaction (see scheme) which affords allylic amines in up to 89 % ee and 91 % yield with a catalyst derived from [Ni(cod)2] and a P-chiral ferrocenyl phosphane (e.g. 1). The coupling products are easily deprotected to enantiomerically enriched, tetrasubstituted primary allylic amines, which can be recrystallized to optical purity.